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Egregiously corrupt, Loeb openly enjoyed the company of Carmine Falcone and several other of Gotham's "elite," whether criminal or simply rich and apathetic. He hired then-Lieutenant James Gordon to the force, expecting that he would fall into line, especially after being partnered with Loeb's equally corrupt suboordinate, Arnold Flass. When Gordon turns out to be an officer of integrity, Loeb expresses disappointment, but his hands are tied because several of Gordon's acts have been covered by the press and made him a public hero.

When Batman first appeared, Loeb denied Gordon's requests for a manhunt. In his opinion, Batman was helping to maintain order in Gotham by taking care of low-level criminals. Moreover, Loeb felt that Batman's popularity with the public was all to the good, as it gave them false hope and kept them distracted from the activities of more sophisticated criminals like Falcone.

That opinion changed when Batman crashed a sumptuous banquet hosted by Gotham's wealthy (with Loeb and several underworld figures in attendance) and told them that he intended to take them down as well. Batman also threw down the gauntlet to Falcone by invading his mansion, tying him up, and driving his favorite Rolls-Royce into a lake.

Enraged, Loeb ordered Gordon to arrest Batman immediately, and authorizes a massive task force. However, the vigilante proved frustratingly elusive, until the police cornered him in an abandoned building. Loeb ordered a bomb dropped on the building, after which a SWAT unit conducted an armed search of the rubble. As morning broke, however, Batman escaped, much to Loeb's aggravation.

When Gordon began to side with Batman against the corrupt GCPD, Loeb tried to blackmail him with evidence of his extramarital affair with Sgt. Sarah Essen. The attempt was unsuccessful, as Gordon had decided to admit the truth to his wife, and ask Essen to leave Gotham.

Eventually, Batman, Gordon, and District Attorney Harvey Dent exposed Loeb's ties to the Falcone mob, and he was forced to resign. Another corrupt officer, Grogan, replaced him. Gordon became the Department's commissioner a few years later.

In Batman: Dark Victory, Loeb returned, hoping to use the Hangman killings as an excuse to try to get the city council to remove Gordon as Commissioner. Believing that he, and not Gordon, understands the way Gotham "really" works, he has enough ego to think he can regain his former position. However, before his plans were fulfilled, he became a victim of the Hangman Killer himself.

Commissioner Loeb makes his debut in "What the Little Bird Told Him", where he is briefed on the Electrocutioner's activities in Gotham after escaping Arkham Asylum. He later is convinced by Gordon to let him track down and arrest Electrocutioner in a 24 hour time limit, with Gordon getting his badge back if he succeeds. Gordon, despite lying about knowing Electrocutioner's moves, nonetheless succeeds and gets his badge back, with Gordon also making a subtle threat to him about taking his badge away. He is also mentioned in "Welcome Back Jim Gordon" by Harvey Bullock, where he reveals that Loeb is one of the people of high positions who are involved in Arnold Flass's drug dealing activities on the side. He later has a more antagonistic role in "Everybody Has a Cobblepot", as he ended up forcing Harvey Bullock to recant his testimony of Arnold Flass's murder against a witness to release Flass as well as nominate him for the Police Union president with the threat of blackmail about an undercover operation that went south where Bullock had to choose between his informant's life and his own. It is also revealed that he has blackmail material for everyone in not only the GCPD, but also pretty much everyone in the infrastructure of the city, and has ties to Alberto Falcone. He later tries to have Gordon and Harvey Dent killed by a Chinese mob he was connected to after his partner lured them there in a trap. It was also rumored that twenty years prior, Loeb's wife had died from falling down the stairs by his hand, although it was later revealed that Loeb's only role was covering up the murder and the actual murderer was his unhinged daughter Miriam Loeb. He then agreed for supply Bullock's file (unwilling to supply all the files as Falcone would kill him otherwise), having a fair retrial for Arnold Flass, and nominate Gordon for possible Police Union president in exchange for Gordon keeping silent about his discovery about Miriam and her role in her mother's death.